{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T03:04:51Z","timestamp":1790651091620,"version":"4.1.0"},"reference-count":47,"publisher":"Wiley","issue":"35","license":[{"start":{"date-parts":[[2017,5,31]],"date-time":"2017-05-31T00:00:00Z","timestamp":1496188800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2017,6,22]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Prolinol\u2013phosphine chiral ligands enabled highly enantioselective copper\u2010catalyzed intermolecular alkyne\u2013nitrone coupling (Kinugasa reaction) to produce 1,3,4\u2010trisubstituted chiral \u03b2\u2010lactams. A high level of enantiocontrol was achieved not only with aryl\u2010 or alkenylacetylenes but also with alkylacetylenes, which were important but unfavorable substrates in the previously reported protocols. Two\u2010point hydrogen bonding between the chiral ligand and the nitrone oxyanion consisting of O\u2212H\u22c5\u22c5\u22c5O and C(sp<jats:sup>3<\/jats:sup>)\u2212H\u22c5\u22c5\u22c5O hydrogen bonds is proposed.<\/jats:p>","DOI":"10.1002\/chem.201702070","type":"journal-article","created":{"date-parts":[[2017,5,9]],"date-time":"2017-05-09T22:52:47Z","timestamp":1494370367000},"page":"8400-8404","source":"Crossref","is-referenced-by-count":47,"title":["Asymmetric Synthesis of \u03b2\u2010Lactams through Copper\u2010Catalyzed Alkyne\u2013Nitrone Coupling with a Prolinol\u2013Phosphine Chiral Ligand"],"prefix":"10.1002","volume":"23","author":[{"given":"Yurie","family":"Takayama","sequence":"first","affiliation":[{"name":"Department of Chemistry Faculty of Science Hokkaido University  Sapporo 060-0810 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Takaoki","family":"Ishii","sequence":"additional","affiliation":[{"name":"Department of Chemistry Faculty of Science Hokkaido University  Sapporo 060-0810 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hirohisa","family":"Ohmiya","sequence":"additional","affiliation":[{"name":"Department of Chemistry Faculty of Science Hokkaido University  Sapporo 060-0810 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tomohiro","family":"Iwai","sequence":"additional","affiliation":[{"name":"Department of Chemistry Faculty of Science Hokkaido University  Sapporo 060-0810 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8435-9624","authenticated-orcid":false,"given":"Martin C.","family":"Schwarzer","sequence":"additional","affiliation":[{"name":"Institute of Quantum Beam Science Ibaraki University  Mito, Ibaraki 310-8512 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Seiji","family":"Mori","sequence":"additional","affiliation":[{"name":"Institute of Quantum Beam Science Ibaraki University  Mito, Ibaraki 310-8512 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tohru","family":"Taniguchi","sequence":"additional","affiliation":[{"name":"Frontier Research Center for Advanced Material and Life Science Faculty of Advanced Life Science Hokkaido University  Sapporo 060-0810 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kenji","family":"Monde","sequence":"additional","affiliation":[{"name":"Frontier Research Center for Advanced Material and Life Science Faculty of Advanced Life Science Hokkaido University  Sapporo 060-0810 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8770-2982","authenticated-orcid":false,"given":"Masaya","family":"Sawamura","sequence":"additional","affiliation":[{"name":"Department of Chemistry Faculty of Science Hokkaido University  Sapporo 060-0810 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2017,5,31]]},"reference":[{"key":"e_1_2_2_1_1","unstructured":"For books on the biological activity of \u03b2-lactams see:"},{"key":"e_1_2_2_2_2","volume-title":"The Chemistry of \u03b2-Lactams","year":"1992"},{"key":"e_1_2_2_3_2","volume-title":"Chemistry and Biology of \u03b2-Lactam Antibiotics, Vol. 1\u20133","year":"1982"},{"key":"e_1_2_2_4_1","unstructured":"For books on the synthetic chemistry of \u03b2-lactams see:"},{"key":"e_1_2_2_5_2","volume-title":"Synthesis of \u03b2-Lactam Antibiotics: Chemistry, Biocatalysis and Process Integration","year":"2001"},{"key":"e_1_2_2_6_2","volume-title":"Enantioselective Synthesis of \u03b2-Amino Acids","year":"1997"},{"key":"e_1_2_2_7_2","volume-title":"The Organic Chemistry of \u03b2-Lactams","year":"1993"},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr4005549"},{"key":"e_1_2_2_9_1","doi-asserted-by":"publisher","DOI":"10.1039\/c39720000466"},{"key":"e_1_2_2_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00121a018"},{"key":"e_1_2_2_11_1","unstructured":"For reviews on the asymmetric Kinugasa reaction see:"},{"key":"e_1_2_2_12_2","doi-asserted-by":"publisher","DOI":"10.1039\/b607819m"},{"key":"e_1_2_2_13_2","first-page":"2321","author":"Pal R.","year":"2007","journal-title":"Synlett"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr078371m"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2014.06.024"},{"key":"e_1_2_2_16_1","unstructured":"\u00a0"},{"key":"e_1_2_2_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja025833z"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200352103"},{"key":"e_1_2_2_18_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200352103"},{"key":"e_1_2_2_19_2","doi-asserted-by":"publisher","DOI":"10.1039\/b306653c"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2012.04.049"},{"key":"e_1_2_2_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo0602874"},{"key":"e_1_2_2_22_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201204373"},{"key":"e_1_2_2_23_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2009.06.050"},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2007.01.006"},{"key":"e_1_2_2_25_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201301114"},{"key":"e_1_2_2_26_1","unstructured":"For diastereoselective Kinugasa reactions see:"},{"key":"e_1_2_2_27_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0032-1316732"},{"key":"e_1_2_2_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol801257j"},{"key":"e_1_2_2_29_1","unstructured":"For selected reports on the synthesis of \u03b2-lactam cholesterol absorption inhibitors and their biological activities:"},{"key":"e_1_2_2_30_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(94)85308-8"},{"key":"e_1_2_2_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo990428k"},{"key":"e_1_2_2_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm030283g"},{"key":"e_1_2_2_33_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00041a033"},{"key":"e_1_2_2_34_1","unstructured":"\u00a0"},{"key":"e_1_2_2_35_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201301280"},{"key":"e_1_2_2_36_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol701534n"},{"key":"e_1_2_2_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/om800667c"},{"key":"e_1_2_2_38_1","unstructured":"\u00a0"},{"key":"e_1_2_2_39_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3ob40828k"},{"key":"e_1_2_2_40_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja991795g"},{"key":"e_1_2_2_41_2","doi-asserted-by":"publisher","DOI":"10.1006\/jmbi.1998.2199"},{"key":"e_1_2_2_42_2","doi-asserted-by":"publisher","DOI":"10.1006\/jmbi.1995.0492"},{"key":"e_1_2_2_43_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo5029198"},{"key":"e_1_2_2_44_1","doi-asserted-by":"publisher","DOI":"10.1366\/11-06321"},{"key":"e_1_2_2_45_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo502838p"},{"key":"e_1_2_2_46_1","unstructured":"The difficulty in the previously described asymmetric Kinugasa reactions of alkylacetylenes may have been due to existence of stepwise heterocycle formation pathways. Without a hydrogen-bonding site in the catalyst enantiodiscrimination for acyclic C\u2212C-bond-forming transition states should be more difficult than that for concerted [3+2] cycloaddition transition states."}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.201702070","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.201702070","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T16:44:14Z","timestamp":1760287454000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.201702070"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2017,5,31]]},"references-count":47,"journal-issue":{"issue":"35","published-print":{"date-parts":[[2017,6,22]]}},"alternative-id":["10.1002\/chem.201702070"],"URL":"https:\/\/doi.org\/10.1002\/chem.201702070","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2017,5,31]]}}}